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Staging a fashion show in a country that still has food rationing was always going to be contentious. Compared with President Hollande’s visit in May 2015, during which he urged the USA to lift its 50-year embargo of Cuba, or President Obama’s in March of this year (the one man with the power to do something about the blockade, or ‘el bloqueo’, as it is known colloquially on the island), the benefits to the country of Chanel’s visitation were less obvious.

After almost 60 years of isolation, suddenly it seems as though everyone’s arriving in Cuba at once. On the coat-tails of Obama, Conan O’Brien, one of America’s biggest chat-show hosts, filmed a series of comedy skits in Havana, including one in which he and his trademark red quiff investigate one of the city’s super-markets and mock the meagre array of stock – somewhat insensitively, you might think, given the circumstances. Where there’s a trend brewing, the Kardashians are never far behind. Sure enough, they arrived, with a camera crew, to film scenes for their reality show during the Chanel festivities.

President Barack Obama in Cuba.Credit:
Getty

Why Chanel chose Cuba

Chanel knew nothing of these trips when it began planning its Cruise show 14 months ago. ‘Karl Lagerfeld just thought it would be an inspiring, invigorating place for the design team to see,’ says Bruno Pavlovsky, the brand’s president of fashion and the man charged with making financial sense of these (on paper) financially insane productions. ‘It’s really not about a financial transaction for us. We’re not going to be selling here for a very long time to come, if ever. It’s a question of Chanel being culturally engaged with the world. We’ve had Chanel in Seoul, Chanel in Salzburg, Chanel in Dallas…’

None of these provided quite the same cultural dissonances as Cuba, I suggest. ‘True,’ Palovsky acknowledges, ‘and we wanted to work with that. We deliberately didn’t want to fly in chefs from France, or impose our ideas on the hotels here. Initially we thought that we wouldn’t actually be able to come to Cuba – that it would be more of a concept than a geographical reality, like when we did a Chanel-Bombay show in Paris. But the Cuban government was keen. They invited us.’

Fashion is actually a good fit for the Cuban revolutionaries

Could it be that fashion is the Cuban revolutionaries’ weak spot? It was Alberto Korda’s 1960 black and white portrait of the young revolutionary as a brooding heart-throb that turned Che Guevara into a global pin-up (his image is still ubiquitous in Cuba) and made the beret, that quintessential emblem of Left Bank Parisian chic, a symbol for armchair communists the world over – memorably satirised in the 1970s BBC sitcom Citizen Smith. President Raúl Castro’s granddaughter studied fashion in Paris and even interned at Vogue Paris, or so a Cuban designer tells me with authority.

I can’t find confirmation of this, but then the Castros have form when it comes to controlling inconvenient news. More flagrantly, Fidel Castro’s own grandson Tony Castro – an Alice-band-wearing, Cara Delevingne-browed 19-year-old – is a sometime model who, to the glee of the international press, was rumoured to have been booked to appear in the Chanel Cuba show.

Models on the runway at Chanel's show in Havana.Credit:
Chanel

Except that he wasn’t among the handful of Cuban models who walked in the show alongside international stars such as Stella Tennant, Lindsey Wixson, Mariacarla Boscono and Binx Walton, all of them wearing luxurious, eclectic colours and prints – how Cuba’s elite might dress, if it existed. Nor, according to Pavlovsky, had Castro junior ever been up for discussion. ‘The rumours,’ reflected Pavlovsky, as we sipped strong Cuban coffee in the garden of Havana’s Teatro Martí the morning before the show, ‘have been wild.’ He did not look unhappy – although he might have been irked to read reports the day after the show stating that Cubans had been barred from it, thanks to Chanel’s very own bloqueo around the Paseo del Prado. These were followed by a leak that a group of Cuban architects had penned a letter following Chanel’s after-show party to complain about the takeover of the historic plaza behind Havana’s cathedral.

It took a dedicated team four months to find a site for the show

It is true that not every single one of Cuba’s 11 million inhabitants was invited, any more than all of France’s 66 million residents are ushered into Chanel’s regular shows in Paris. It’s a matter of crowd control. ‘But we were very specific that we wanted the show to be in the open air so that many more people could see it than we could seat,’ Pavlovsky says. In that regard, mission accomplished.

Classic cars carry guests to the Chanel show in Havana.Credit:
Alamy

Having been designed by a Frenchman in the 1770s, Paseo del Prado is perhaps the most naturally perfect open-air catwalk in the world. Besides being lined with pastel colonial mansions – and the occasional brutalist block – it incorporates a 170m tiled promenade: ideal flâneur material. Chanel was abetted in its search for the location by the team it fielded to its Central and South American HQ in Panama for four months on recces, and by Eusebio Leal, the 73-year-old director of restoration in Old Havana, who pushed for it to be made a Unesco World Heritage Site in 1982.

The runway on Havana's Paseo del PradoCredit:
Reuters

Celebrities descend on Havana

While 170 vintage American convertibles growled along the Paseo, horns not so much hooting as serenading as they deposited some 700 guests, Cubans waved, cheered and blew whistles from the balconies and roofs of mansions along the tree-fringed boulevard. Tilda Swinton, Gisele Bündchen, Vanessa Paradis, the editor of Portuguese Vogue – one got the distinct impression they were one and the same to the Cubans, although Vin Diesel, who was in Cuba filming Fast 8, earnt an extra-loud roar.

Actor Vin Diesel waves to spectators on the way to the Chanel show.Credit:
Rex

Given that, as one local told me, most Cubans have only the haziest concept of what Chanel, or any other luxury fashion brand, is (Adidas and Nike have more currency at the moment), their enthusiasm bespeaks a collective good nature, along with a willingness to party at the slightest excuse.

Cuba's grand, faded beauty

Cuba is not a quiet society. There are groups of besuited, dapper old men and ruffle-skirted women performing their own versions of Buena Vista Social Club on every other street corner and in many bars and cafes. Is it for the tourists? Undoubtedly. But the locals enjoy it too.

The loudness begins with those gorgeously nostalgic Technicolor cars. How, in a nation of shortages, do people acquire those lime-green, cerulean and daffodil car paints? ‘By accident,’ Michel, my guide, tells me. ‘In the 1950s, the colours would have been more conventional, but over the years the cars’ owners had to take what paint they could get.’

Gisele Bundchen at the Chanel Cruise showCredit:
Reuters

All of Havana’s grand, faded beauty has a wild makeshift defiance, like a Southern belle teetering in the gutter with her skirts hoicked up. Perhaps it was always like this. ‘To live in Havana,’ wrote Graham Greene in 1958, when Ava Gardner and the Rat Pack were regulars, ‘was to live in a factory that turned out human beauty on a conveyor belt.’ Even now, when the sartorial pickings are meagre, when stonewashed leggings and frosted nail varnishes are about the sum of it, there’s no missing that Cuban carriage, bordering on swagger.

As for the spectacular architecture – it has acquired an extra half-century’s patina of drama and deprivation. For every loving, Unesco-funded restoration, there are another 20 or 30 buildings in a state of post-apocalyptic decay. Colonnaded mansions have become tenements, their plaster long since worn away; roofs rotted; balconies hanging on by little more than bolts and prayers; trees sprouting internally, poking through broken windows; flaking doors offering glimpses of dark interiors lit (when the power is working) by flickering television screens. Imminent collapse is a constant, genuine concern.

Classic cars queue to collect guests for the Chanel show in HavanaCredit:
Alamy

The weather provides a reprieve of sorts – most of the time it’s so hot, life happens on the street. There are times, however, when entire neighbourhoods seem deserted, their buildings so dilapidated that, as another journalist told me, the last time she saw devastation on this scale she was in a war-torn African country.

Weirdly, it’s all ridiculously photogenic.

The most fashionable restaurant in town

And it knows it. La Guarida, Havana’s most fashionable restaurant, is located on the second floor of an imposing early-20th-century mansion in an iffy part of Central Havana. It is wildly popular, at least with foreigners – at $100 for two, its prices are way beyond most Cubans’ purchasing power. This is where Obama, Jack Nicholson, Rihanna, Beyoncé, Jay Z, Steven Spielberg, Pedro Almodóvar and yes, Conan O’Brien, have all eaten, and there are framed photos to prove it. Yet while the restaurant itself is a warren of cosy, chandelier-lit rooms and French windows, the first two floors resemble a bombed-out shell where the only clues to habitation are a grand staircase and two washing lines belonging to the ground-floor tenants.

Attendees and onlookers wait for the show to begin.Credit:
AP Photo

"It's Latino communism"

At times it can seem as though Habaneros, and certainly the tourists, are fetishising the decay. Yet this is not the dour communism I saw in East Berlin and Moscow in the 1980s. ‘It’s Latino communism,’ says Pamela Ruiz, a Colombian American who has lived in Havana with her artist husband since 1995. ‘They would consider it more as socialism.’ Ruiz, who was at the Chanel show, spied her dream house in 1999, a 19th-century villa in one of Havana’s beachside suburbs. Its owners had fled in 1959, leaving their housekeeper in charge. A clause in Cuba’s fiendishly complicated property laws meant that while the housekeeper owned it, she couldn’t sell to Ruiz, only exchange with her. ‘I didn’t have a place that she wanted to move to,’ Ruiz recalls.

A band plays at the Chanel show in Havana.Credit:
Getty

It took a further seven years for Ruiz to find another couple who agreed to swap their apartment with her, enabling her, finally, to swap with the housekeeper. Ruiz’s reward is a stunning period house she has rescued from flooding and fly-tipping and filled with mid-20th-century gems, with a garden large enough to host art festivals that now attract busloads of American collectors.

She must be one of few to have made the reverse journey to Cuba in the 1990s, I say. Even now, the shoreline around the island is eerily empty: Cubans aren’t allowed to own boats in case they make a break for Florida.

‘I think I may have been the only one,’ she says. ‘It was impossible to immigrate to Cuba at that time. The government just couldn’t compute it.’

As the Soviet Union began to collapse in 1989, Cuba lost its main life support. Fidel Castro introduced the Special Period – a brazen euphemism for a time when many people in Cuba didn’t have enough to eat. Life remains tough. A medical doctor earns $60 a month. The average Cuban salary is closer to $20. There are still plenty of very skinny folk begging in the street, many of them elderly.

Fidel Castro and Raul Castro in 1993.Credit:
AP Photo

But there are also glimpses of socialism as the early revolutionary idealists might have imagined it. This is a society that feels comfortable allowing its children to hitch to and from school. Or maybe there just aren’t any school buses. Meanwhile, at the government-owned Cohiba cigar factory, a meticulously maintained primrose-coloured mansion in a suburb once dominated by lushly landscaped country clubs, the workers decide each week which novels they want to be read to them through their headphones by a narrator on the ground floor. Chanel’s design team has global excursions; Cohiba’s tobacco-leaf rollers, communal stories.

Cubans in conflict

'As an artist, I benefit from selling my work to foreigners,’ Alexandre Arrechea, a Cuban artist, tells me one morning. ‘But as a Cuban and a black man I want to see real change happen in my country, not the type of superficial change that foreigners are perceiving.'

Arrechea, who splits his time between Madrid, New York and, increasingly, the apartment where I visit him in Havana, isn't alone in having mixed feelings about his homeland.

This sense of impending regret that Cuba, on the cusp of rejoining the rest of the world, may lose more than it gains, is a refrain I hear often – from Cubans who spend part of their time abroad. The trickle of 25,000 visitors a year has swelled to three million. The Adonia, the first cruise ship to sail to the country from the USA in more than 50 years, docked in Havana the day before Chanel’s show, and the Starwood hotel group recently announced plans to operate three luxury hotels in Havana. If it can make the existing state-owned ‘five-star’ hotels in Havana, including the once-glamorous Hotel Nacional, with its magnificent art deco, Moroccan-inspired lobby and Soviet-inspired rooms and food, raise their game, while creating more jobs, that may be no bad thing.

Models on the Chanel runway in Havana.Credit:
Getty

Other imports will be seen as more questionable. The night a group of British journalists went to La Guarida, for instance, the Kardashian clan, filming for their reality show, bumped us from our table. The next day, at Cuba’s other ‘best’ restaurant, they arrived, camera crew in tow, on the terrace where we were having lunch. Bemused by the entourage and cameras, the Cubans seemed blissfully unaware of who they actually were.

Chanel coming to Cuba is a good thing

The ignorance won’t last. At the studio of Jorge Torres and Larry J González, two Cuban satirical artists who work together under the name jorge & larry, Anna Wintour has been immortalised in ink, alongside montages of fashion shows. Torres’s family owned department stores before the revolution. ‘Chanel coming to Havana has to be a good thing,’ he says. ‘It’s a show of support and of course it’s a political act. Fashion always is. It’s about economics and status.’

A video posted by Lisa Armstrong (@misslisaarmstrong) on May 3, 2016 at 11:02pm PDT

It is too early to see whether Cuba will establish a fashion industry alongside its burgeoning art culture. This is a society living largely hand to mouth. ‘We’ve lost most of our craft tradition,’ Arrechea says. There are entrepreneurial shoots sprouting all over the country, however – small craft workshops; privately run restaurants and bed and breakfasts in people’s homes, which are generally far more enticing than the dispiriting state-owned concerns. For these to flourish, Cuba, which bans most advertising (except for the government), must ignite in its socialist-reared population a desire for life’s non-essentials.

‘Will you be taking your shower gel when you leave?’ The hotel maid pointed at the bottles Chanel had placed in all its guests’ bathrooms and beamed with an intensity that left no doubt as to the hoped-for answer. This, it turned out, was a scene being played out on every floor. When I told her she could have the lot, she kissed me. That yearning for the trappings of status – when was it ever hard to ignite?